Patent EA-003923-B1 (EA)
Title: Cyclopentenones, process for preparing the same, and the use thereof
Inventor: KOYAMA NOBUTO
IPC: C07C49/707
Filed: 1997-09-01
Abstract: 1. A method of manufacturing 4,5-dihydroxy-2-cyclopenten-1-one represented by the following formula [1] which is characterized in that at least one substance selected from the following (a), (b) and (c) is heated, wherein (a): uronic acid or uronic acid derivative(s); (b): a saccharide compound which contains uronic acid and/or uronic acid derivative(s); and (c): a substance containing a saccharide compound which contains uronic acid and/or uronic acid derivative(s). 2. A method of manufacturing 4,5-dihydroxy-2-cyclopenten-1-one which is characterized in that at least one substance selected from the following (a), (b) and (c) is heated and the 4,5-dihydroxy-2-cyclopenten-1-one represented by the formula [1] is collected from the above heat-treated product, wherein (a): uronic acid or uronic acid derivative(s); (b): a saccharide compound which contains uronic acid and/or uronic acid derivative (s); and (c): a substance containing a saccharide compound which contains uronic acid and/or uronic acid derivative(s). 3. A method of manufacturing 4,5-dihydroxy-2-cyclopenten-1-one according to claim 1 or 2 wherein uronic acid is galacturonic acid, glucuronic acid, guluronic acid, mannuronic acid and/or iduronic acid. 4. A method of manufacturing 4,5-dihydroxy-2-cyclopenten-1-one according to claim 1 or 2 wherein uronic acid derivative is salt of uronic acid, or uronic acid lactone, uronic acid ester, uronic acid amide or salt thereof. 5. A method of manufacturing 4,5-dihydroxy-2-cyclopenten-1-one according to claim 1 or 2 wherein the saccharide compound is a saccharide compound which is selected from pectin, pectic acid, alginic acid, hyaluronic acid, heparin, heparan sulfate, fucoidan, chondroitin sulfate, chondroitin, dermatan sulfate and/or decomposed product thereof. 6. A method of manufacturing 4,5-dihydroxy-2-cyclopenten-1-one according to any of claims 1-5 wherein the heat-treated product is obtained by heating at 60-350 degree C for several seconds to several days. 7. A method of manufacturing 4,5-dihydroxy-2-cyclopenten-1-one according to any of claims 1-6 wherein the heat-treated product is obtained by heating under acidic to neutral conditions. 8. A method of manufacturing an optically active compound of 4,5-dihydroxy-2-cyclopenten-1-one which is characterized in including the following steps: (A): a step wherein at least one substance selected from the following (a), (b) and (c) is heated to produce 4,5-dihydroxy- 2-cyclopenten-1-one, wherein (a): uronic acid or uronic acid derivative(s), (b): a saccharide compound which contains uronic acid and/or uronic acid derivative(s), and (c): a substance containing a saccharide compound which contains uronic acid and/or uronic acid derivative(s); (B): an optional step wherein 4,5-dihydroxy-2-cyclopenten-1-one is isolated from the resulting heat-treated product; and (C): a step where 4,5-dihydroxy-2-cyclopenten-1-one is subjected to an optical resolution. 9. A method of manufacturing an optically active compound of 4,5-dihydroxy-2-cyclopenten-1-one according to claim 8 wherein uronic acid is galacturonic acid, glucuronic acid, guluronic acid, mannuronic acid and/or iduronic acid. 10. A method of manufacturing an optically active compound of 4,5-dihydroxy-2-cyclopenten-1-one according to claim 8 wherein uronic acid derivative is salt of uronic acid, or uronic acid lactone, uronic acid ester, uronic acid amide or salt thereof. 11. A method of manufacturing an optically active compound of 4,5-dihydroxy-2-cyclopenten-1-one according to claim 8 wherein the saccharide compound is a saccharide compound which is selected from pectin, pectic acid, alginic acid, hyaluronic acid, heparin, heparan sulfate, fucoidan, chondroitin sulfate, chondroitin, dermatan sulfate and/or decomposed product thereof. 12. A method of manufacturing an optically active compound of 4,5-dihydroxy-2-cyclopenten-1-one according to any of claims 8-11 wherein the heat-treated product is obtained by heating at 60-350 degree C for several seconds to several days. 13. A method of manufacturing an optically active compound of 4,5-dihydroxy-2-cyclopenten-1-one according to any of claims 8-12 wherein the heat-treated product is obtained by heating under acidic to neutral conditions. 14. The (-)-4,5-dihydroxy-2-cyclopenten-1-one having an optical rotation [alpha]D<20> -105 degree (c = 0.53, ethanol). 15. The (+)-4,5-dihydroxy-2-cyclopenten-1-one having an optical rotation [alpha]D<20> +104 degree (c = 0.53, ethanol). 16. An anticancer agent which is characterized in containing 4,5-dihydroxy-2-cyclopenten-1-one represented by the formula [1] and/or an optically active compound thereof as the anticancer agent. 17. A cancer cell differentiation inducer which is characterized in containing 4,5-dihydroxy-2-cyclopenten-1-one represented by the formula [1] and/or an optically active compound thereof as the cancer cell differentiation inducer. 18. An apoptosis inducer which is characterized in containing 4,5-dihydroxy-2-cyclopenten-1-one represented by the formula [1] and/or an optically active compound thereof as the apoptosis inducer. 19. Use of the heat-treated product selected from the following (a), (b) and (c) is heated, wherein (a): uronic acid or uronic acid derivative(s); (b): a saccharide compound which contains uronic acid and/or uronic acid derivative(s); and (c): a substance containing a saccharide compound which contains uronic acid and/or uronic acid derivative(s), as the anticancer agent. 20. Use of the heat-treated product selected from the following (a), (b) and (c) is heated, wherein (a): uronic acid or uronic acid derivative(s); (b): a saccharide compound which contains uronic acid and/or uronic acid derivative(s); and (c): a substance containing a saccharide compound which contains uronic acid and/or uronic acid derivative(s), as the cancer cell differentiation inducer. 21. Use of the heat-treated product selected from the following (a), (b) and (c) is heated, wherein (a): uronic acid or uronic acid derivative(s); (b): a saccharide compound which contains uronic acid and/or uronic acid derivative(s); and (c): a substance containing a saccharide compound which contains uronic acid and/or uronic acid derivative(s), as the apoptosis inducer. 22. A method for the induction of cancer cell differentiation which is characterized in using 4,5-dihydroxy-2-cyclopenten-1-one represented by the formula [1] and/or an optically active compound thereof as effective ingredient(s). 23. A method for the induction of apoptosis which is characterized in using 4,5-dihydroxy-2-cyclopenten-1-one represented by the formula [1] and/or an optically active compound as effective ingredient(s). 24. The method according to claim 22 or 23 which is characterized in using 4,5-dihydroxy-2-cyclopenten-1-one represented by the formula [1] obtained by the method according to claim 1 or an optically active compound thereof. 25. The method according to claim 22 or 23 which is characterized in using the heat-treated product according to claim 1. 26. The method according to claim 22 or 23 which is characterized in using 4,5-dihydroxy-2-cyclopenten-1-one represented by the formula [1] obtained by the method according to claim 2. 27. A method for preparing food or beverage which is characterized in that 4,5-dihydroxy-2-cyclopenten-1-one represented by the formula [1] and/or an optically active compound thereof are/is contained therein, diluted thereby and/or added thereto. 28. The method according to claim 27 which is characterized in that 4,5-dihydroxy-2-cyclopenten-1-one represented by the formula [1] obtained by the method according to claim 1. 29. The method according to claim 27 which is characterized in that the heat-treated product according to claim 1 is contained therein, diluted thereby and/or added thereto. 30. The method according to claim 27 which is characterized in that 4,5-dihydroxy-2-cyclopenten-1-one represented by the formula [1] obtained by the method according to claim 2 is contained therein, diluted thereby and/or added thereto. 31. The method according to any of claim 27-30 which is characterized in that 4,5-dihydroxy-2-cyclopenten-1-one represented by the formula [1] and/or an optically active compound thereof is contained in an amount of 5 x 10<-6> parts or more per 100 parts of food or beverage. 32. the method according to any of claim 37-32 which is an anticancer food and/or an anticancer beverage. 33. An intermediate for manufacturing 4,5-dihydroxy-2-cyclopenten-1-one represented by the following formula [1] based on materials selected from plants, animals or microorganisms, which contains a saccharide compound containing uronic acid and/or uronic acid derivative(s), characterized in that the intermediate is obtained by the dry heating treatment at 60-400 degree C or by the protease treatment.